1,4-Dioxane → 6-Methyl-2,4-bis-methylsulfanylpyridin-3-ylamine

HRID 2379629Notes

Reaction equation

HRID 2379629 reaction equation
[N+:1]([C:4]1[C:5]([S:13][CH3:14])=[N:6][C:7]([CH3:12])=[CH:8][C:9]=1[S:10][CH3:11])([O-])=O.O1CCOCC1.[H][H]>[Ni].CO>[NH2:1][C:4]1[C:5]([S:13][CH3:14])=[N:6][C:7]([CH3:12])=[CH:8][C:9]=1[S:10][CH3:11]

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 100368396-methyl-2,4-bis(methylthio)-3-nitroPyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 99903926-Methyl-2,4-bis-methylsulfanylpyridin-3-ylamineYield 85%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 18.9 g (0.082 mol) 3-nitro-2,4-bis(methylthio)-6-methylpyridine and 18.9 g Raney nickel in 600 ml. 1,4-dioxane and 300 ml methanol was shaken with hydrogen (15 psi) in a Parr hydrogenation apparatus for 3.5 hr. The catalyst was filtered and the filtrate was concentrated to dryness in vacuo. The solid residue was chromatographed on silica gel (650g), eluting with 9:1 hexane/ethyl acetate to yield 14.0 g. (85% yield) of the title compound as an off-white solid.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated to dryness in vacuo
  3. customThe solid residue was chromatographed on silica gel (650g)
  4. washeluting with 9:1 hexane/ethyl acetate
  5. customto yield 14.0 g

Sources & evidence

ORD record
ord-2a303b22ca964089949aa572281a2f9f
Source dataset
uspto-grants-1994_11
Patent number
US05362878

Reaction notes

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